Tonight with your 13 to 17 year old
The prompt
“What's a job or path that excites you, even if it seems like a long shot?”
What to listen for
If they answer readily and with energy, that's a sign they feel safe enough to dream big around you without worrying you'll immediately talk them out of it, which is exactly the reaction you want to protect by staying curious rather than practical tonight.
If they preface it with "this is probably dumb but," reassure them gently that you're just curious, not judging feasibility, and then actually don't pivot the conversation to feasibility.
If they say they don't know yet, that's completely normal at this age, you could ask what kind of day-to-day they'd want, regardless of job title, as a softer entry point.
What this tells you
This tells you what excites them enough to imagine a future around it, independent of what seems safe or realistic to adults.